Acyl derivatives of 4, 4&#39;-diamino diphenyl oxide



Patented Mar. 7,

UNETED STATES r orF cEF] nnnnsr r. Gn-ErHER, on MIDLAND, MICHIGAN, 'Asfsrsivon. T0 'rHEDow CHEMICAL 1;:

CQMPANY, or MIDLAND, MICEEGAN, A conronarron or MICHIGAN AGYL DERIVATIVES 0F 4,4-DI.A 'MINO DIPHENYL OXIDE No Drawing.

The present invention relates to acyl derivatives of'aromatic amino-ethers, and has regard more particularly to compounds of the foregoing character which are derived from L F-diamino diphenyl oxide.

In medicine certain derivatives of paraamino phenol ethers have found a more or less extensive use on account of their antipyretic, antineuralgic and analgesic properties. The most important compounds of this type are the phenetidins, the latter being the acyl derivatives of para-phenetidin, or ethoxy-para-amino phenol. Examples of the foregoing are acetphenetidin, triphenin and lactophenin, which are, respectively, the acetyl, propionyl and lactyl derivatives of para-phenetidin.

I have found that similar derivatives of 4:,4J-diamino diphenyl oxide may be prepared which possess therapeutic, as well as chemical,

properties more or less analogous to those of the aforesaid para-phenetidin derivatives.

The relationship between lfl diamino diphenyl oxide and para-phenetidin, and hence the acyl derivatives thereof, is seen from a comparison of their respective constitutional formulae, viz

(4) NH C H OC H NH (4) 4,4-(1iamino diphenyl oxide (4) NH2C6H4OC2H para-phenetidin My invention comprises the new class of compounds formed by acylating one, or both. of the amino groups of the aforesaid 4, 1- diamino diphenyl oxide. I have found that such acyl derivatives may be prepared in the usual way by treating the diamino-et-her with 1 organic acids or the corresponding acid anhydrides. With the latter the reaction takes place without addition of heat, Whereas when an acid is used refluxing for a time with heating to about 100 C. or higher, will generally be required to complete the reaction.

Example 1 V The 4,4-formyl-diamino diphenyl oxide is formed by refluxing the diamino-ether with an excess of formic acid. The solid product is precipitated in the reaction mix-- Application filed. January 15, 1930. Serial No. 421,061. A

ture as formed from which it is filtered and recrystallized fromdilute, e. g."5Q percent, alcohol. Fine colorless crystals, slightly soluble in hot water, insoluble incold water.

P. 154; C. Formula;

Example 2 com r eo i acetic anhydride, or by refluxing with glacial acetic acid. Colorless, lustrous crystal flakes,

s11 ghtly soluble in hot water. M. P. 228-229 The dipropionyl. derivative is formed I similarly by reaction with propionic'anhydride o r acid..v Fine colorless silky needles, very sllghtly soluble in hot water. M. P. 253 Cir-Formula, 'v ,7 G;H5G .N O6

The dilactyl derivative is formed by heata I 7 mg the diamino-ether with lactic acid. Fine Instead of reacting 1 mole of the diamine with the corresponding aliphatic or aromatic acids or acid anhydrides, e. g. tartaric, citric,

benzoic, phthalic acids and the like, as well as substituted derivatives thereof.

Gther modes of applying the principle of my invention may be employed instead of those explained, change being made as to the materials employed,- provided the compounds stated by any of the following claims or the equivalent of such stated compounds be obtained. H

I therefore particularly point out and distinctly claim as my invention 4 1. As a newproduct, a compound having the following formula v wherein X may be H or the same acyl group.

2. As a new product, 4,4l-diacylamido diphenyl oxide.

3. As a new product, a'compound having the following formula.

wherein X may be H or the formyl group, HOO-. i

4. As a new product, 4,4J-diformanido di- A phenyl oxide.

5. As a new product, a compound having the following formula 7 wherein X may be H or the acetyl roup, CH CO. g

6. As a new product, l,l' diphenyl oxide.

7. As a new product, a compound having the following formula -diacetylamidowherein X may be H or the lactyl group,

CH OHOHCO 8. As a new diphenyl oxide.

Signed by me, this 11 day of January, 1930.

ERNEST F. GRETHER,

product, 4,4f-di1acty1amido- 

